Phosphorus oxychloride → 4-Chloro-6-(5-methyl-1,3,4-oxadiazol-2-yl)quinazoline

HRID 1936754Notes

Reaction equation

HRID 1936754 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][NH:11][C:10]3=O)=[N:4][N:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:5]3[O:6][C:2]([CH3:1])=[N:3][N:4]=3)[CH:8]=2)[N:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357038826-(5-Methyl-1,3,4-oxadiazol-2-yl)quinazolin-4-one

Product 1

HCID 226097254-Chloro-6-(5-methyl-1,3,4-oxadiazol-2-yl)quinazoline

Procedure

6-(5-Methyl-1,3,4-oxadiazol-2-yl)quinazolin-4-one (0.3 g) was treated with phosphorus oxychloride at reflux under N2 for 5 hours. The mixture was concentrated in vacuo and the residue azeotroped with toluene. This was then taken up in ethyl acetate and washed with 5% sodium bicarbonate and saturated brine, dried over magnesium sulphate and concentrated in vacuo to give the title compound (0.22 g) as a yellow solid; δH [2H6]DMSO 12.65 (1H,bs), 8.71(1H,d), 8.45 (1H,dd), 8.33 (1H,s), 7.95 (1H,s) 2.73 (3H,s).

Workup

  1. temperatureat reflux under N2 for 5 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue azeotroped with toluene
  4. washwashed with 5% sodium bicarbonate and saturated brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22bf8213514a4263a909de7fbc65bce8
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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